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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:56:29 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034146
Secondary Accession Numbers
  • HMDB34146
Metabolite Identification
Common NameOctadecanamide
DescriptionOctadecanamide, also known as stearamide or kemamide S, belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group). Thus, octadecanamide is considered to be a fatty amide. Octadecanamide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Octadecanamide.
Structure
Data?1563862518
Synonyms
ValueSource
StearamideChEBI
Stearic acid amideChEBI
Stearate amideGenerator
Kemamide SMeSH
Adogen 42HMDB
Advawax 290HMDB
Amide C-18HMDB
Amide C18HMDB
Amide tHMDB
Armid 18HMDB
Crodamide SHMDB
Crodamide S, SRHMDB
KemamidesHMDB
OctadecamideHMDB
OctadecylamideHMDB
Petrac vyn-ezeHMDB
Stearic amideHMDB
StearoylamideHMDB
StearoylamineHMDB
StearylamideHMDB
Uniwax 1750HMDB
Chemical FormulaC18H37NO
Average Molecular Weight283.4925
Monoisotopic Molecular Weight283.287514811
IUPAC Nameoctadecanamide
Traditional Namestearamide
CAS Registry Number124-26-5
SMILES
CCCCCCCCCCCCCCCCCC(N)=O
InChI Identifier
InChI=1S/C18H37NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H2,19,20)
InChI KeyLYRFLYHAGKPMFH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point109 °CNot Available
Boiling Point408.23 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.029 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP7.292 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.5e-05 g/LALOGPS
logP7.87ALOGPS
logP6.34ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)16.88ChemAxon
pKa (Strongest Basic)-0.58ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity88.11 m³·mol⁻¹ChemAxon
Polarizability39.03 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.70631661259
DarkChem[M-H]-175.43231661259
DeepCCS[M+H]+180.31630932474
DeepCCS[M-H]-176.29630932474
DeepCCS[M-2H]-213.38530932474
DeepCCS[M+Na]+189.28530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OctadecanamideCCCCCCCCCCCCCCCCCC(N)=O3345.0Standard polar33892256
OctadecanamideCCCCCCCCCCCCCCCCCC(N)=O2340.0Standard non polar33892256
OctadecanamideCCCCCCCCCCCCCCCCCC(N)=O2398.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octadecanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C2433.7Semi standard non polar33892256
Octadecanamide,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C2344.2Standard non polar33892256
Octadecanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2549.1Semi standard non polar33892256
Octadecanamide,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C2504.2Standard non polar33892256
Octadecanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C(C)(C)C2637.6Semi standard non polar33892256
Octadecanamide,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N[Si](C)(C)C(C)(C)C2550.5Standard non polar33892256
Octadecanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2976.4Semi standard non polar33892256
Octadecanamide,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2850.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Octadecanamide EI-B (Non-derivatized)splash10-0a4i-9000000000-9e0257218bfc5bd50b102017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Octadecanamide EI-B (Non-derivatized)splash10-0a4i-9000000000-9e0257218bfc5bd50b102018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9530000000-42eda07ab8c72ac6e50c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octadecanamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 10V, Positive-QTOFsplash10-00lr-0090000000-1560eb3762d94248b8d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 20V, Positive-QTOFsplash10-014i-3490000000-056500efdc623f7358362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 40V, Positive-QTOFsplash10-052f-9820000000-fe010a6e498b39c6aa462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 10V, Negative-QTOFsplash10-001i-0090000000-54b38622810aab5d71db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 20V, Negative-QTOFsplash10-001l-4090000000-6511b8bb0a98ff7442da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 40V, Negative-QTOFsplash10-0006-9000000000-5236e5b7ee4530fe52d22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 10V, Negative-QTOFsplash10-001i-0090000000-884c21ca7a2ca039448b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 20V, Negative-QTOFsplash10-0006-9040000000-f16395fa98d1e40ea2f82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 10V, Positive-QTOFsplash10-001i-2090000000-c81ca37d7799cd429fc22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 20V, Positive-QTOFsplash10-05o0-9270000000-4b6969535f00eeaa2e382021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octadecanamide 40V, Positive-QTOFsplash10-0a4l-9000000000-a5fdb3c3f4095d7ab5c02021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012421
KNApSAcK IDC00037572
Chemspider ID29032
KEGG Compound IDC13846
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound31292
PDB IDNot Available
ChEBI ID34900
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1270391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.